CA2294342C - Procede de synthetisation d'intermediaires de carbapenem a chaine laterale - Google Patents

Procede de synthetisation d'intermediaires de carbapenem a chaine laterale Download PDF

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Publication number
CA2294342C
CA2294342C CA002294342A CA2294342A CA2294342C CA 2294342 C CA2294342 C CA 2294342C CA 002294342 A CA002294342 A CA 002294342A CA 2294342 A CA2294342 A CA 2294342A CA 2294342 C CA2294342 C CA 2294342C
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CA
Canada
Prior art keywords
compound
formula
accordance
produce
reacted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA002294342A
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English (en)
Other versions
CA2294342A1 (fr
Inventor
Karel M. J. Brands
John M. Williams
Ulf H. Dolling
Ronald B. Jobson
Antony J. Davies
Ian F. Cottrell
Mark Cameron
Michael S. Ashwood
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Sharp and Dohme LLC
Original Assignee
Merck and Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from GBGB9810184.3A external-priority patent/GB9810184D0/en
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of CA2294342A1 publication Critical patent/CA2294342A1/fr
Application granted granted Critical
Publication of CA2294342C publication Critical patent/CA2294342C/fr
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pyrrole Compounds (AREA)

Abstract

L'invention concerne un procédé de synthétisation d'un composé de formule (1). Un composé de formule (2) est mis à réagir tout d'abord avec un chlorure diphénylphosphinique, afin d'activer le groupe acide carboxylique, puis avec un chlorure méthanesufonyle, afin de produire un composé de formule (4). Ce composé de formule (4) est ensuite mis à réagir avec une source de sulfure d'un métal de groupe II dans de l'eau, afin de produire un composé de formule (1).
CA002294342A 1997-07-09 1998-07-02 Procede de synthetisation d'intermediaires de carbapenem a chaine laterale Expired - Fee Related CA2294342C (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US5203297P 1997-07-09 1997-07-09
US60/052,032 1997-07-09
GBGB9810184.3A GB9810184D0 (en) 1998-05-13 1998-05-13 Process for synthisizing carbapenem side chain intermediates
GB9810184.3 1998-05-13
PCT/US1998/013738 WO1999002531A1 (fr) 1997-07-09 1998-07-02 Procede de synthetisation d'intermediaires de carbapenem a chaine laterale

Publications (2)

Publication Number Publication Date
CA2294342A1 CA2294342A1 (fr) 1999-01-21
CA2294342C true CA2294342C (fr) 2006-03-14

Family

ID=26313663

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002294342A Expired - Fee Related CA2294342C (fr) 1997-07-09 1998-07-02 Procede de synthetisation d'intermediaires de carbapenem a chaine laterale

Country Status (5)

Country Link
EP (1) EP1019411A4 (fr)
JP (1) JP2002504156A (fr)
AU (1) AU731586B2 (fr)
CA (1) CA2294342C (fr)
WO (1) WO1999002531A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999002492A1 (fr) * 1997-07-10 1999-01-21 Merck & Co., Inc. Formes cristallines d'intermediaires a chaine laterale antibiotiques
EP1261612A4 (fr) * 2000-03-01 2003-04-02 Merck & Co Inc Formes cristallines d'intermediaires a chaines laterales pour des antibiotiques
TWI290925B (en) * 2000-11-20 2007-12-11 Sankyo Co Production of carbapenem antimicrobial agent
MX2007001713A (es) * 2004-08-11 2007-07-13 Donald L Barbeau Compuestos farmaceuticos no cardiotoxicos.
CN102264744A (zh) * 2008-12-25 2011-11-30 株式会社钟化 碳青霉烯侧链中间体的改良制造方法
CN106565579A (zh) * 2016-06-26 2017-04-19 宁夏海诚电化信息科技有限公司 一种尔它培南侧链生产工艺
CN117304203A (zh) * 2023-09-28 2023-12-29 郑州原理生物科技有限公司 一种美罗培南侧链中间体硫醇内酯的制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4340738A (en) * 1979-06-21 1982-07-20 Janssen Pharmaceutica, N.V. 2,3-Dihydro-imidazo[2,1-b]benzothiazoles
AU644008B2 (en) * 1990-08-10 1993-12-02 Sumitomo Pharmaceuticals Company, Limited Beta-lactam compounds, and their production and use
JP3091297B2 (ja) * 1992-01-10 2000-09-25 住友製薬株式会社 ピロリジン誘導体およびその製造方法
JP3112952B2 (ja) * 1995-08-04 2000-11-27 メルク エンド カンパニー インコーポレーテッド カルバペネム側鎖中間体の合成方法

Also Published As

Publication number Publication date
JP2002504156A (ja) 2002-02-05
AU731586B2 (en) 2001-04-05
EP1019411A4 (fr) 2003-08-13
AU8282198A (en) 1999-02-08
EP1019411A1 (fr) 2000-07-19
CA2294342A1 (fr) 1999-01-21
WO1999002531A1 (fr) 1999-01-21

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